ruthenium trichloride; sodium periodate; sodium hydrogencarbonate in acetonitrile T=40 - 45°C; 68 h; Product distribution; Further Variations:TemperaturesReagentsreaction times;

Decaborane; palladium on activated charcoal in methanol T=20°C; 7 h;

[Mo(CO)3(acetonitrile)3] in methanol T=130°C; SonicationMicrowave irradiationInert atmosphere; chemoselective reaction;

1: N-(tert-butoxycarbonyl)-α-(phenylsulfonyl)-C-naphthalen-2-yl-methylamine With TMS-SnBu3; cesium fluoride in N,N-dimethyl-formamide T=20°C; 0.0833333 h; Inert atmosphere; 2: carbon dioxide in N,N-dimethyl-formamide T=100°C; P=7500.75 Torr; 3 h; Autoclave; 3: diazomethane Further stages;

1: N-(tert-butoxycarbonyl)-α-(phenylsulfonyl)-C-naphthalen-2-yl-methylamine With TMS-SnBu3; cesium fluoride in N,N-dimethyl-formamide T=20°C; 0.0833333 h; Inert atmosphere; 2: carbon dioxide in N,N-dimethyl-formamide T=100°C; P=7500.75 Torr; 3 h; Autoclave; 3: With hydrogenchloride in diethyl ether; water; N,N-dimethyl-formamide pH=2; Inert atmosphere;

sodium carbonate in 1,4-dioxane; water T=0 - 20°C;

trifluoroacetic acid in dichloromethane T=20°C; 3 h;

1: 5.38 g / PPh3; DEAD / tetrahydrofuran / 22 h / 0 - 20 °C 2: NaBH4; AcOH / propan-1-ol; H2O / 5 h / 80 - 90 °C 3: 1.43 g / Na2CO3 / dioxane; H2O / 0 - 20 °C View Scheme

1: NaBH4; AcOH / propan-1-ol; H2O / 5 h / 80 - 90 °C 2: 1.43 g / Na2CO3 / dioxane; H2O / 0 - 20 °C View Scheme

1: 93 percent / K2CO3; TBAB / tetrahydrofuran / 20 °C 2: TFA / CH2Cl2 / 3 h / 20 °C View Scheme